L-AZC | CAS#2133-34-8 | L-proline amino acid derivative

MedKoo Cat#: 463782 | Name: L-AZC

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

L-Azetidine-2-carboxylic acid is a non-proteinogenic amino acid derivative of L-proline that has been found in C. majalis and has diverse biological activities. It is toxic to a variety of bacteria, but the bacteria E. agglomerans and E. amnigenus metabolize it for use as a source of nitrogen. L-Azetidine-2-carboxylic acid induces misfolding of proteins when incorporated into the nascent polypeptide chain. It destabilizes the collagen triple helix and reduces the extracellular localization of collagen.2 L-Azetidine-2-carboxylic acid inhibits growth of type IV collagen-producing 450. murine mammary cancer cells in vitro but is inactive in a 450.1 murine model of mammary cancer when administered at doses ranging from 12.5 to 200 mg/kg twice per day and induces liver toxicity at the highest dose. It is teratogenic to, and disrupts skeletal development in, hamster fetuses when administered to pregnant hamsters at a dose of 300 mg/kg on gestational day 11.

Chemical Structure

L-AZC

CAS#2133-34-8

Theoretical Analysis

MedKoo Cat#: 463782

Name: L-AZC

CAS#: 2133-34-8

Chemical Formula: C4H7NO2

Exact Mass: 101.0477

Molecular Weight: 101.11

Elemental Analysis: C, 47.52; H, 6.98; N, 13.85; O, 31.65

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
2g	USD 350.00	2 Weeks
5g	USD 650.00	2 Weeks
10g	USD 950.00	2 Weeks

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Synonym

L-AZC; L AZC; LAZC; L-Azetidine-2-carboxylic Acid; A2C; Aze; LACA; (S)-(–)-Azetidine-2-carboxylic Acid;

IUPAC/Chemical Name

(S)-azetidine-2-carboxylic acid

InChi Key

IADUEWIQBXOCDZ-VKHMYHEASA-N

InChi Code

InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1

SMILES Code

OC([C@@H]1CCN1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

L-Azetidine-2-carboxylic acid is an endogenous metabolite.

In vitro activity:

AZE (L-Azetidine-2-carboxylic acid) (at concentrations > 1000 µM) significantly reduced cell viability, increased BAX/Bcl2 ratio and caused cell death. Collectively, these data indicate that AZE-induced toxicity is associated with increased pro-inflammatory activity and reduced survival in BV2 microglia. Reference: Curr Issues Mol Biol. 2022 Sep 28;44(10):4500-4516. https://pubmed.ncbi.nlm.nih.gov/36286023/

In vivo activity:

The teratogenic effects of L-azetidine-2-carboxylic acid (LACA) were evaluated in hamsters. Subcutaneous hemorrhage and cleft palate were the most frequently occurring externally visible defects. Skeletal anomalies such as retarded ossification, synchronous vertebral ossification and shortening of bones were found in a high percentage of LACA-treated fetuses. The major teratological effect of LACA appeared to be the retardation of skeletal development. Reference: Teratology. 1981 Jun;23(3):365-72. https://pubmed.ncbi.nlm.nih.gov/7256659/

	Solvent	mg/mL	mM
Solubility
	PBS (pH 7.2)	1.0	9.89
	Water	100.0	989.07

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 101.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Piper JA, Jansen MI, Thomas Broome S, Rodgers KJ, Musumeci G, Castorina A. Pro-Inflammatory and Pro-Apoptotic Effects of the Non-Protein Amino Acid L-Azetidine-2-Carboxylic Acid in BV2 Microglial Cells. Curr Issues Mol Biol. 2022 Sep 28;44(10):4500-4516. doi: 10.3390/cimb44100308. PMID: 36286023; PMCID: PMC9600089. 2. Han L, Zhao W, Li A, Zhou B, Zhang J, Wu W. Antifungal activity of l-azetidine-2-carboxylic acid isolated from Disporopsis aspera rhizomes against Podosphaera xanthii. Pest Manag Sci. 2022 May;78(5):1946-1952. doi: 10.1002/ps.6812. Epub 2022 Feb 10. PMID: 35085420. 3. Klohs WD, Steinkampf RW, Wicha MS, Mertus AE, Tunac JB, Leopold WR. Collagen-production inhibitors evaluated as antitumor agents. J Natl Cancer Inst. 1985 Aug;75(2):353-9. PMID: 3860688. 4. Joneja MG. Teratogenic effects of proline analogue L-azetidine-2-carboxylic acid in hamster fetuses. Teratology. 1981 Jun;23(3):365-72. doi: 10.1002/tera.1420230311. PMID: 7256659.

In vitro protocol:

In vivo protocol:

1. Klohs WD, Steinkampf RW, Wicha MS, Mertus AE, Tunac JB, Leopold WR. Collagen-production inhibitors evaluated as antitumor agents. J Natl Cancer Inst. 1985 Aug;75(2):353-9. PMID: 3860688. 2. Joneja MG. Teratogenic effects of proline analogue L-azetidine-2-carboxylic acid in hamster fetuses. Teratology. 1981 Jun;23(3):365-72. doi: 10.1002/tera.1420230311. PMID: 7256659.

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A 9 bp cis-element in the promoters of class I small heat shock protein genes on chromosome 3 in rice mediates L-azetidine-2-carboxylic acid and heat shock responses. J Exp Bot. 2010 Oct;61(15):4249-61. doi: 10.1093/jxb/erq230. Epub 2010 Jul 19. PMID: 20643810; PMCID: PMC2955743. 16: Tsai FY, Zhang XH, Ulanov A, Widholm JM. The application of the yeast N-acetyltransferase MPR1 gene and the proline analogue L-azetidine-2-carboxylic acid as a selectable marker system for plant transformation. J Exp Bot. 2010 Jun;61(10):2561-73. doi: 10.1093/jxb/erq086. Epub 2010 Apr 28. PMID: 20430752; PMCID: PMC2882255. 17: Ishchuk OP, Abbas CA, Sibirny AA. Heterologous expression of Saccharomyces cerevisiae MPR1 gene confers tolerance to ethanol and L: -azetidine-2-carboxylic acid in Hansenula polymorpha. J Ind Microbiol Biotechnol. 2010 Feb;37(2):213-8. doi: 10.1007/s10295-009-0674-0. Epub 2009 Dec 5. PMID: 19967446. 18: Cameron PH, Chevet E, Pluquet O, Thomas DY, Bergeron JJ. 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